Travelers have found it’s best to book a flight 61 days in advance to save up to 80% compared to booking the same week of travel. As your travel date approaches, the cost of this flight route may potentially increase. While opting to book 61 days out may not be an option for all, there are still additional ways to secure a deal in the near future. You might find a flight from Illinois to Key West 1-2 weeks in advance for as low as $355, or $408 for flights within the next 24 hours.
Our data shows that August tends to be the cheapest month to fly to Key West from Illinois. Users have commonly found prices around $452 for the month, but tickets can be as low as $226. Due to multiple factors, prepare for potentially higher prices in March.
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Illinois to Key West as you normally would.
Fly from
Fly to
Budget
$195 - $309
Route
Depart
Return
Price
Chicago O'Hare IntlKey West
ORD - EYW
ORDEYW
Chicago O'Hare Intl
Sat 8/10
1 stop5h 41m
Key West
Wed 8/14
1 stop8h 06m
Chicago O'Hare IntlKey West
ORD - EYW
ORDEYW
Chicago O'Hare Intl
Wed 9/4
1 stop7h 37m
Key West
Tue 9/10
1 stop7h 21m
Chicago O'Hare IntlKey West
ORD - EYW
ORDEYW
Chicago O'Hare Intl
Wed 9/4
1 stop6h 10m
Key West
Wed 9/11
1 stop6h 33m
Chicago O'Hare IntlKey West
ORD - EYW
ORDEYW
Chicago O'Hare Intl
Wed 9/4
1 stop7h 37m
Key West
Tue 9/10
2 stops6h 35m
Chicago O'Hare IntlKey West
ORD - EYW
ORDEYW
Chicago O'Hare Intl
Wed 8/21
1 stop5h 35m
Key West
Thu 8/29
1 stop6h 46m
Chicago MidwayKey West
MDW - EYW
MDWEYW
Chicago Midway
Tue 6/4
1 stop5h 58m
Key West
Tue 6/11
1 stop4h 46m
Chicago O'Hare IntlKey West
ORD - EYW
ORDEYW
Chicago O'Hare Intl
Tue 7/9
1 stop4h 47m
Key West
Wed 7/17
1 stop7h 31m
Chicago O'Hare IntlKey West
ORD - EYW
ORDEYW
Chicago O'Hare Intl
Fri 5/31
1 stop6h 11m
Key West
Fri 6/7
1 stop6h 56m
Chicago O'Hare IntlKey West
ORD - EYW
ORDEYW
Chicago O'Hare Intl
Fri 11/1
Nonstop3h 10m
Key West
Mon 11/4
Nonstop3h 24m
No data available for this route at this time. Please check back soon.
Food
Entertainment
Boarding
Comfort
Overall
Crew
Reviews
When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
Food
Entertainment
Boarding
Comfort
Overall
Crew
Reviews
When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
Food
Entertainment
Boarding
Comfort
Overall
Crew
Reviews
When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
Food
Entertainment
Boarding
Comfort
Overall
Crew
Reviews
When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
Cheapflights goes through 900+ travel sites to look for the best flight deals for flights from Illinois to Key West. Too many options? Cheapflights also provides filters for things like airlines, price ranges, and number of stops to help you make a decision easily.
Cheapflights helps you find that perfect flight to Key West from Illinois by searching from hundreds of airlines and agencies you know and love. We are also free to use, in case you were wondering!
Users can book flights with no change fees policies with our dedicated filters. Book flights from Illinois to Key West flexibly with Cheapflights today.
Not ready to book yet? You can track prices for flights from Illinois to Key West on Cheapflights with our Price Alert feature and get notified when better prices are available.